# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shrv248
_database_code_depnum_ccdc_archive 'CCDC 983225'
_audit_update_record             
;
2015-02-10 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;

_audit_creation_date             2013-08-01
_audit_creation_method           'from SHELXTL CIF, local template and enCIFer'
_chemical_name_systematic        
; 
 4H-1,2,4-triazol-4-amine 3,6-dinitro-1,4-dihydropyrazolo[4,3-c]pyrazole 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C2 H4 N4), C4 H2 N6 O4'
_chemical_formula_sum            'C8 H10 N14 O4'
_chemical_formula_weight         366.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4207(13)
_cell_length_b                   6.797(2)
_cell_length_c                   10.530(3)
_cell_angle_alpha                82.822(5)
_cell_angle_beta                 77.868(3)
_cell_angle_gamma                71.330(3)
_cell_volume                     358.62(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             188
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2008/1 (Bruker, 2008)'
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_T_max  0.9916

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3234
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         26.43
_reflns_number_total             1460
_reflns_number_gt                1298
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_cell_refinement       'Bruker APEX2 v2010.3-0 (Bruker, 2009)'
_computing_data_reduction        
;
Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008)
;
_computing_structure_solution    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_structure_refinement  'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL v2008/4 (Bruker, 2008)'
_computing_publication_material  'Bruker SHELXTL v2008/4 (Bruker, 2008)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0375P)²+0.1667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1460
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.1687(2) 0.03072(18) 0.34633(11) 0.0171(3) Uani 1 1 d . . .
H1 H 1.1642 0.0923 0.2678 0.021 Uiso 1 1 calc R . .
N2 N 1.3844(2) -0.10702(18) 0.38459(11) 0.0183(3) Uani 1 1 d . . .
C3 C 1.3091(3) -0.1632(2) 0.50895(13) 0.0169(3) Uani 1 1 d . . .
C4 C 1.0412(3) -0.0611(2) 0.55366(12) 0.0160(3) Uani 1 1 d . . .
N5 N 1.4931(2) -0.30783(18) 0.58092(11) 0.0195(3) Uani 1 1 d . . .
O6 O 1.7217(2) -0.38708(17) 0.52592(11) 0.0268(3) Uani 1 1 d . . .
O7 O 1.4066(2) -0.34327(18) 0.69641(10) 0.0285(3) Uani 1 1 d . . .
N8 N 0.4222(2) 0.24647(19) 1.03269(11) 0.0197(3) Uani 1 1 d . . .
N9 N 0.1900(2) 0.20955(18) 1.10045(11) 0.0189(3) Uani 1 1 d . . .
C10 C 0.0323(3) 0.2337(2) 1.01721(13) 0.0174(3) Uani 1 1 d . . .
H10 H -0.1394 0.2171 1.0379 0.021 Uiso 1 1 calc R . .
N11 N 0.1507(2) 0.28571(18) 0.89786(11) 0.0165(3) Uani 1 1 d . . .
C12 C 0.3915(3) 0.2927(2) 0.91202(13) 0.0183(3) Uani 1 1 d . . .
H12 H 0.5192 0.3265 0.8436 0.022 Uiso 1 1 calc R . .
N13 N 0.0353(3) 0.3225(2) 0.78502(12) 0.0221(3) Uani 1 1 d . . .
H13A H 0.165(4) 0.274(3) 0.7183(18) 0.027 Uiso 1 1 d . . .
H13B H -0.020(3) 0.459(3) 0.7697(17) 0.027 Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.3448(16) . ?
N1 C4 1.3588(17) 2_756 ?
N1 H1 0.8800 . ?
N2 C3 1.3332(18) . ?
C3 C4 1.4005(18) . ?
C3 N5 1.4280(18) . ?
C4 N1 1.3588(17) 2_756 ?
C4 C4 1.381(3) 2_756 ?
N5 O6 1.2290(16) . ?
N5 O7 1.2312(16) . ?
N8 C12 1.3025(18) . ?
N8 N9 1.3915(16) . ?
N9 C10 1.3096(18) . ?
C10 N11 1.3458(18) . ?
C10 H10 0.9500 . ?
N11 C12 1.3608(17) . ?
N11 N13 1.4156(16) . ?
C12 H12 0.9500 . ?
N13 H13A 0.893(18) . ?
N13 H13B 0.88(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C4 110.22(11) . 2_756 ?
N2 N1 H1 124.9 . . ?
C4 N1 H1 124.9 2_756 . ?
C3 N2 N1 106.26(11) . . ?
N2 C3 C4 111.43(12) . . ?
N2 C3 N5 120.96(12) . . ?
C4 C3 N5 127.59(12) . . ?
N1 C4 C4 108.36(15) 2_756 2_756 ?
N1 C4 C3 147.91(13) 2_756 . ?
C4 C4 C3 103.73(14) 2_756 . ?
O6 N5 O7 124.67(12) . . ?
O6 N5 C3 119.38(12) . . ?
O7 N5 C3 115.95(11) . . ?
C12 N8 N9 106.36(11) . . ?
C10 N9 N8 107.82(11) . . ?
N9 C10 N11 109.59(12) . . ?
N9 C10 H10 125.2 . . ?
N11 C10 H10 125.2 . . ?
C10 N11 C12 105.82(11) . . ?
C10 N11 N13 124.31(11) . . ?
C12 N11 N13 129.87(11) . . ?
N8 C12 N11 110.41(12) . . ?
N8 C12 H12 124.8 . . ?
N11 C12 H12 124.8 . . ?
N11 N13 H13A 107.5(11) . . ?
N11 N13 H13B 106.5(11) . . ?
H13A N13 H13B 106.1(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 N2 C3 0.09(14) 2_756 . . . ?
N1 N2 C3 C4 -0.22(15) . . . . ?
N1 N2 C3 N5 -179.23(11) . . . . ?
N2 C3 C4 N1 179.9(2) . . . 2_756 ?
N5 C3 C4 N1 -1.2(3) . . . 2_756 ?
N2 C3 C4 C4 0.26(18) . . . 2_756 ?
N5 C3 C4 C4 179.19(14) . . . 2_756 ?
N2 C3 N5 O6 -2.62(19) . . . . ?
C4 C3 N5 O6 178.54(13) . . . . ?
N2 C3 N5 O7 177.23(12) . . . . ?
C4 C3 N5 O7 -1.6(2) . . . . ?
C12 N8 N9 C10 0.50(15) . . . . ?
N8 N9 C10 N11 -0.25(15) . . . . ?
N9 C10 N11 C12 -0.08(15) . . . . ?
N9 C10 N11 N13 179.73(12) . . . . ?
N9 N8 C12 N11 -0.56(15) . . . . ?
C10 N11 C12 N8 0.41(15) . . . . ?
N13 N11 C12 N8 -179.39(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 N9 0.88 1.84 2.7150(18) 174.4 1_654
N13 H13A N2 0.893(18) 2.419(19) 3.2517(18) 155.2(15) 2_756
N13 H13B N9 0.88(2) 2.591(19) 3.303(2) 138.5(14) 2_567

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.044
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_monostrong
_database_code_depnum_ccdc_archive 'CCDC 1048548'
_audit_update_record             
;
2015-02-10 deposited with the CCDC.
2015-03-17 downloaded from the CCDC.
;
_audit_creation_date             2014-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C2 H4 N4), C4 H2 N6 O4'
_chemical_formula_sum            'C8 H10 N14 O4'
_chemical_formula_weight         366.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.2903(3)
_cell_length_b                   7.2315(3)
_cell_length_c                   15.5555(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.037(2)
_cell_angle_gamma                90
_cell_volume                     707.15(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9845
_cell_measurement_temperature    150
_cell_measurement_theta_max      43.486
_cell_measurement_theta_min      3.11
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.7489
_exptl_absorpt_correction_T_min  0.6915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0568 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.9234.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.720
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25675
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         5.906
_diffrn_ambient_temperature      150
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'TRIUMPH graphite'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1591
_reflns_number_total             1742
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.502
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1742
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.2937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0897
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N4 N 0.42250(15) 0.45644(13) 0.77489(6) 0.0180(2) Uani 1 1 d . . . . .
N5 N 0.56525(15) 0.51773(13) 0.90136(6) 0.0181(2) Uani 1 1 d . . . . .
H5 H 0.646(3) 0.557(2) 0.9448(11) 0.034(4) Uiso 1 1 d . . . . .
N6 N 0.37602(14) 0.42995(13) 0.91764(6) 0.0173(2) Uani 1 1 d . . . . .
N7 N 0.11485(16) 0.29889(16) 0.82288(7) 0.0253(2) Uani 1 1 d . . . . .
H7A H 0.049(3) 0.321(2) 0.7728(12) 0.035(4) Uiso 1 1 d . . . . .
H7B H 0.039(3) 0.278(2) 0.8684(12) 0.034(4) Uiso 1 1 d . . . . .
C3 C 0.58839(17) 0.53187(16) 0.81792(7) 0.0190(2) Uani 1 1 d . . . . .
H3 H 0.709(2) 0.588(2) 0.7938(10) 0.025(4) Uiso 1 1 d . . . . .
C4 C 0.29765(16) 0.39538(15) 0.83902(6) 0.0162(2) Uani 1 1 d . . . . .
O1 O 0.14917(14) 0.69211(12) 0.34740(5) 0.0252(2) Uani 1 1 d . . . . .
O2 O -0.03755(13) 0.78293(13) 0.45491(6) 0.0287(2) Uani 1 1 d . . . . .
N1 N 0.11498(14) 0.70399(13) 0.42462(6) 0.0177(2) Uani 1 1 d . . . . .
N2 N 0.23554(14) 0.60795(12) 0.56541(6) 0.0158(2) Uani 1 1 d . . . . .
N3 N 0.40280(14) 0.51671(12) 0.60073(6) 0.0148(2) Uani 1 1 d . . . . .
H3A H 0.408(3) 0.494(3) 0.6577(13) 0.038(4) Uiso 1 1 d . . . . .
C1 C 0.26794(15) 0.61741(14) 0.48136(6) 0.0140(2) Uani 1 1 d . . . . .
C2 C 0.54101(15) 0.46891(14) 0.53941(6) 0.0128(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N4 C3 1.3359(14) . ?
N4 C4 1.3647(13) . ?
N5 H5 0.877(18) . ?
N5 N6 1.3804(13) . ?
N5 C3 1.3152(14) . ?
N6 C4 1.3261(13) . ?
N7 H7A 0.884(19) . ?
N7 H7B 0.880(19) . ?
N7 C4 1.3608(14) . ?
C3 H3 0.951(16) . ?
O1 N1 1.2308(13) . ?
O2 N1 1.2250(13) . ?
N1 C1 1.4270(13) . ?
N2 N3 1.3428(12) . ?
N2 C1 1.3321(13) . ?
N3 H3A 0.90(2) . ?
N3 C2 1.3579(13) . ?
C1 C2 1.4021(13) 3_666 ?
C2 C1 1.4022(13) 3_666 ?
C2 C2 1.3882(18) 3_666 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N4 C4 103.03(9) . . ?
N6 N5 H5 119.1(11) . . ?
C3 N5 H5 130.8(12) . . ?
C3 N5 N6 110.08(9) . . ?
C4 N6 N5 102.24(8) . . ?
H7A N7 H7B 119.2(17) . . ?
C4 N7 H7A 115.9(12) . . ?
C4 N7 H7B 114.6(12) . . ?
N4 C3 H3 126.7(9) . . ?
N5 C3 N4 110.53(9) . . ?
N5 C3 H3 122.8(9) . . ?
N6 C4 N4 114.11(10) . . ?
N6 C4 N7 123.43(10) . . ?
N7 C4 N4 122.38(10) . . ?
O1 N1 C1 115.83(9) . . ?
O2 N1 O1 125.06(10) . . ?
O2 N1 C1 119.12(10) . . ?
C1 N2 N3 106.37(8) . . ?
N2 N3 H3A 119.5(12) . . ?
N2 N3 C2 110.46(8) . . ?
C2 N3 H3A 130.0(12) . . ?
N2 C1 N1 120.42(9) . . ?
N2 C1 C2 111.44(8) . 3_666 ?
C2 C1 N1 128.13(9) 3_666 . ?
N3 C2 C1 148.28(9) . 3_666 ?
N3 C2 C2 108.11(11) . 3_666 ?
C2 C2 C1 103.61(10) 3_666 3_666 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5 N6 0.877(18) 2.151(18) 2.8518(13) 136.5(15) 3_667
N5 H5 O2 0.877(18) 2.304(18) 2.9777(13) 133.6(14) 4_676
N7 H7A O1 0.884(19) 2.212(19) 3.0765(13) 165.8(16) 3_566
N7 H7B N2 0.880(19) 2.385(19) 3.1712(14) 148.9(16) 2_546
N3 H3A N4 0.90(2) 1.84(2) 2.7425(13) 177.6(18) .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N5 N6 C4 N4 -0.60(12) . . . . ?
N5 N6 C4 N7 176.02(10) . . . . ?
N6 N5 C3 N4 -0.25(13) . . . . ?
C3 N4 C4 N6 0.46(13) . . . . ?
C3 N4 C4 N7 -176.19(11) . . . . ?
C3 N5 N6 C4 0.50(12) . . . . ?
C4 N4 C3 N5 -0.11(12) . . . . ?
O1 N1 C1 N2 -173.91(9) . . . . ?
O1 N1 C1 C2 4.54(15) . . . 3_666 ?
O2 N1 C1 N2 6.03(15) . . . . ?
O2 N1 C1 C2 -175.52(10) . . . 3_666 ?
N2 N3 C2 C1 -179.64(15) . . . 3_666 ?
N2 N3 C2 C2 -0.36(14) . . . 3_666 ?
N3 N2 C1 N1 178.79(9) . . . . ?
N3 N2 C1 C2 0.09(11) . . . 3_666 ?
C1 N2 N3 C2 0.17(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
